Hi @Mike Arias I think it depends on the strategy. 

It looks like a great idea on the surface but the numbers don't stack up from a risk/return point of view as far as I'm concerned (it could be different for you depending on your return expectations).

Depending on your loan it might only work in the STR game.HOA’s normally do not allow in the Oceanside area but if you get on the beach then they do with restrictions.If you want a personal consult let me know.I have a team here in Oceanside, Carlsbad.

I'm trying to make a decision between the two and I wonder if it simply depends on which rep employee you are assigned to in each business, and their experience. 

Not all VA loans are owner-occupied as the VA gives you an allotment so you can have multiple properties with VA loans depending on what they clear you for.

However the most obvious benefit based on what you’re stating is that the depreciation from cost segregation will offset your $100k in taxable income from your commercial rental.There could be more benefits depending on future plans especially if you plan to sell any real estate in the near future. 

Or free up more of your time depending on your goals?

new construction gets valued at a way higher premium. this is a false statement. new construction will always beat existing Very market dependent.

Sometimes, depending on the size of the loan request a board approval is required which could delay the process further depending on how often the board meets. 

STR it will cost you big.this isn't a difficult job depending on the fridge location.